EP4355435A1 - Sulfonatfunktionalisierte alkylpolyglucoside als sulfatfreie tenside für zahnpasta und mundwasser - Google Patents

Sulfonatfunktionalisierte alkylpolyglucoside als sulfatfreie tenside für zahnpasta und mundwasser

Info

Publication number
EP4355435A1
EP4355435A1 EP22825973.5A EP22825973A EP4355435A1 EP 4355435 A1 EP4355435 A1 EP 4355435A1 EP 22825973 A EP22825973 A EP 22825973A EP 4355435 A1 EP4355435 A1 EP 4355435A1
Authority
EP
European Patent Office
Prior art keywords
functionalized alkyl
composition
alkyl polyglucoside
functionalized
polyglucoside
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
EP22825973.5A
Other languages
English (en)
French (fr)
Inventor
Andrew Minczuk
Dennis Abbeduto
Molly MCENERY
Robert N. Comber
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Colonial Chemical Corp
Original Assignee
Colonial Chemical Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Colonial Chemical Corp filed Critical Colonial Chemical Corp
Publication of EP4355435A1 publication Critical patent/EP4355435A1/de
Pending legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60—Sugars; Derivatives thereof
    • A61K8/604—Alkylpolyglycosides; Derivatives thereof, e.g. esters
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • A61Q11/02—Preparations for deodorising, bleaching or disinfecting dentures

Definitions

  • US Published Patent Application No. 2020/0261332 relates to stable anhydrous toothpaste concentrate tablets comprising a binding agent, an abrasive agent, a whitening agent, a polishing agent, a sulfate-free surfactant, natural gum, sweetener, and a flavor agent.
  • US Published Patent Application No. 2020/0121574 is directed to a non alcohol mouthwash composition exhibiting desirable advantages of being alcohol free, being sodium lauryl sulfate free, being gluten free, and being substantially 100% natural, as well as alleviating Xerostomia (dry mouth) by stimulating salivary flow, combatting enamel erosion by providing a means of remineralization, providing anticariogenic activity by acting as an antimicrobial agent, and/or providing anti-inflammatory activity, among other benefits.
  • Alkyl polyglycosides have been used for a number of cleaning applications, including toothpastes and mouthwashes.
  • US Patent no. 5,734,029 is directed to the preparation of improved alkypolyglycoside surfactant mixtures for a variety of end-use applications, including hard surface cleaners, laundry detergents, and personal care products, such as shampoos, soaps, facial cleansers, foam baths, toothpaste, mouthwashes, antiperspirants and the like.
  • the anionic surfactant most commonly used in commercial toothpastes is sodium lauryl sulphate, but other anionic surfactants have also been used and these include sodium dodecylbenzene sulphonate, sodium lauroyl sarcosinate and sodium coconut monoglyceride sulphonate.
  • Surfactants need to be used at levels that provide optimum cleaning, foaming and taste.
  • Scheller, in US Patent No. 4,301, 141 notes that toothpastes need a high enough content of foaming surfactants to achieve minimal optical cleaning control with brushing. Scehller notes that high concentrations of surfactant or wetting agent adversely affects toothpaste flavoring characteristics.
  • the present invention relates to toothpaste and mouthwash compositions containing functionalized alkyl polyglucosides, specifically sulfonated-functionalized alkyl polyglucosides.
  • One aspect of the present invention relates to a functionalized polyglycoside derivative that is made by the crosslinking reaction of a polyglucoside, together with a functionalizing agent that contains a sulfonate group.
  • the preferred polymers are cross-linked, having more than one group per molecule.
  • the sulfonate-functionalized alkyl polyglucosides of the present invention are derived entirely from renewable plant resources and are low-irritation, anionic surfactants with excellent foam and oral toxicity properties.
  • One embodiment of the present invention is an oral care composition
  • a functionalized alkyl polyglucoside surfactant with the ingredients to form of a toothpaste, powder, liquid dentifrice, mouthwash, denture cleanser, chewing gum or candy.
  • the composition comprises a functionalized alkyl polyglucoside surfactant, a toothpaste abrasive, an optional fluoride ingredient, and an optional flavorant.
  • the composition can further comprise at least one of an antibacterial agent, detergent, remineralizer, humectant, anti-calculus agent, sweetener, and an anti-sensitivity agent.
  • the functionalized alkyl polyglucoside is one or more of the following functionalized alkyl polyglucosides: quaternary functionalized alkyl polyglucoside, poly quaternary functionalized alkyl polyglucosides, sulfonated functionalized alkyl polyglucoside, poly sulfonate functionalized alkyl polyglucoside, phosphate functionalized alkyl polyglucosides, poly phosphate functionalized alkyl polyglucosides, betaine functionalized alkyl polyglucosides, poly betaine functionalized alkyl polyglucosides, sulfosuccinate functionalized alkyl polyglucosides, poly sulfosuccinate functionalized alkyl polyglucosides, and citrate functionalized alkyl polyglucoside.
  • the functionalized alkyl polyglucoside includes the following structures, as a mixture: wherein:
  • R is an alkyl chain having 8 to 22 carbon atoms
  • R 1 , R 2 , R 3 , R 4 R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 are independently selected from the group consisting of: -CH 2 -C(0)-0 ' M + , or -C(0)CH 2 -C(0)-0 ' M +
  • R 12 is selected from the group consisting of:
  • R 1A is CH 3 -(CH 2 ) n - ;
  • M is a charge balancing group selected from H, Na, K, or NH4 + ; and n is an integer from 0-36; and positional isomers thereof.
  • the functionalized alkyl polyglucoside is a cross-linked functionalized alkyl polyglucoside.
  • the cross-linked functionalized alkyl polyglucoside has the following structures, as a mixture:
  • R is an alkyl chain having 8 to 22 carbon atoms; a crosslinking agent; and a functionalizing agent selected from:
  • R 1A is CH 3 (CH 2 ) n -;
  • M is a charge balancing group selected from H, Na, K, or NH4 + ; and n is an integer from 0-36; and positional isomers thereof.
  • the crosslinking agent may be chosen from epichlorohydrin, or Cl-CH2-CH(OH)-
  • the functionalized alkyl polyglucoside is a sulfonate- functionalized alkyl polyglucoside.
  • An example of a sulfonate-functionalized alkyl polyglucoside is a compound of the following formula: wherein:
  • R is an alkyl chain; n is between 1 to about 3, and particularly 1.5; and positional isomers thereof.
  • the sulfonate-functionalized alkyl polyglucoside is chosen from sodium laurylglucoside hydroxypropyl sulfonate, sodium declyglucosides hydroxypropyl sulfonate, and combinations thereof.
  • the functionalized alkyl polyglucoside is a polysulfonate-functionalized alkyl polyglucoside.
  • One example is a sodium hydroxypropyl sulfonate laurylglucoside crosspolymer.
  • the polysulfonate-functionalized alkyl polyglucoside is of the following formula: wherein R is an alkyl group having from about 8 to about 22 carbon atoms and n is an integer ranging from 4 to 6; and positional isomers thereof.
  • the functionalized alkyl polyglucoside is a cross polymer of with an sorbitan ester.
  • an sorbitan ester is a cross polymer of with an sorbitan ester.
  • One example is a sorbitan oleate decylglucoside crosspolymer.
  • cross polymer is represented as compounds of the following formulae, and positional isomers thereof, as a mixture: wherein; R is alkyl having 8 to 22 carbon atoms; and wherein:
  • R is alkyl having 8 to 22 carbon atoms; and (c) a sorbitan ester of the following structure: wherein:
  • R 1B is alkyl having 7 to 21 carbons; a crosslinking agent of the following structure in water; and positional isomers thereof.
  • compositions of the invention may further include may known oral care ingredients.
  • the composition may include at least one of abrasives, binders, flavoring agents, coloring agents, humectants, surfactants, fluoride ion sources, anti-calculus agents, alcohol and sweeteners.
  • the derivatized polyglucoside of the present invention comprises a monosaccharide unit, a disaccharide unit, a linker, and a functionalizing agent.
  • At least one functionalized alkyl polyglucoside may be used.
  • two, three, four, or more functional alkyl polyglucosides may be blended to comprise the functionalized alkyl polyglucoside component of the cleaning composition of the present invention.
  • a derivatized alkyl polyglucoside composition of the present invention includes the following, as a mixture:
  • R is an alkyl chain having 8 to 22 carbon atoms
  • R 1 , R 2 , R 3 , R 4 R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 are independently selected from the group consisting of: -CH 2 -C(0)-0 ' M + , or -C(0)CH 2 -C(0)-0-M + and H, with the proviso that R 1 -R 1 1 are not all H;
  • R 12 is selected from the group consisting of:
  • R 1A is CH 3 -(CH 2 )n- ;
  • M is a charge balancing group selected from H, Na, K, or NH4 + ; and n is an integer from 0-36; and positional isomers thereof.
  • the derivatized polyglucoside of the present invention comprises a monosaccharide unit, a disaccharide unit, a crosslinking agent, and a functionalizing agent.
  • a derivatized alkyl polyglucoside composition of the present invention includes the following, as a mixture:
  • R is an alkyl chain having 8 to 22 carbon atoms; a crosslinking agent; and a functionalizing agent selected from: , C1-CH 2 -CH(0H)-S0 3 M, C1-CH 2 -CH(0H)-S0 4 M,
  • R 1A is CH 3 (CH 2 )n-;
  • M is a charge balancing group selected from H, Na, K, or NH4 + ; and n is an integer from 0-36; and positional isomers thereof.
  • the inventive toothpaste or mouthwash surfactant is one that is disclosed in US Patent No. 6,627,612, incorporated herein by reference and sold by Colonial Chemical, Inc. under the brand name Suga ® Nate 160NC, described as sodium laurylglucosides hydroxypropyl sulfonate, a 100% biobased surfactant.
  • the inventive toothpaste or mouthwash surfactant is one that is disclosed in US Patent No. 7,507,399, incorporated herein by reference and sold by Colonial Chemical, Inc. under the brand name Poly Suga ® Nate 160P NC, described as sodium hydroxypropyl sulfonate laurylglucoside crosspolymer.
  • the inventive toothpaste or mouthwash surfactants are those disclosed in US Patent No. 8,268,766, incorporated herein by reference and sold by Colonial Chemical, Inc. under the brand names Poly Suga ® Mulse D6 and Poly Suga ® Mulse D9, both described as sorbitan oleate decylglucoside crosspolymer.
  • the inventive toothpaste or mouthwash surfactant is one that is disclosed in US Patent No. 6,762,289, incorporated herein by reference and sold by Colonial Chemical, Inc. under the brand name Poly Suga ® Sil, described as PEG-8 PG-Coco Glucoside Dimethicone.
  • the inventive toothpaste or mouthwash surfactant is disclosed in PCT application PCT/US20/62184 describing Citrate- Functionalized Polymeric Surfactants Based Upon Alkyl Polyglucosides, incorporated herein by reference and sold by Colonial Chemical, Inc. under the brand name SugaCitrate L1C, described as Disodium Laurylglucosides Hydroxypropyl Citrate.
  • Suga ® Nate 160NC described as sodium laurylglucosides hydroxypropyl sulfonate, is disclosed in US Patent No. 6,627,612 and is one of a class of sulfonate-functionalized alkyl polyglucosides whose general structure is shown below.
  • R is an alkyl chain having 8 to 22 carbon atoms
  • R 1 , R 2 , R 3 , R 4 R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 are independently selected from the group consisting of: and H, with the proviso that R 1 -R 11 are not all H;
  • R 12 is selected from the group consisting of:
  • -S0 3 -M + , and - SO4 -2 M + M is a charge balancing group selected from H, Na, K, or NH4 +
  • Suga ® Nate 160NC is sold as a 40% solution in water but is also sold as
  • a number of functionalized APG’ s are described in the following patents: sulfonate derivatized alkyl polyglucosides (US Patent No. 6,627,612, surfactants sold by Colonial Chemical, Inc. under the brand names Suga ® Nate), phosphate derivatized alkyl polyglucosides (US Patent No. 6,627,612, surfactants sold by Colonial Chemical, Inc. under the brand names Suga ® Fax) amphoteric glycinate derivatized alkyl polyglucosides (US Patent No.
  • derivatized alkyl polyglucosides include polysulfonate derivatized alkyl polyglucosides (US Patent No. 7,507,399, surfactants sold by Colonial Chemical, Inc. under the brand names Poly Suga ® Nates), polyphosphate derivatized alkyl polyglucoside (US Patent No. 7,507,399, surfactants sold by Colonial Chemical, Inc. under the brand names Poly Suga ® Phos) polyquatemary derivatized alkyl polyglucosides (US Patent No. 7,507,399, surfactants sold by Colonial Chemical, Inc.
  • PCT Application PCT/US20/53150 Blends of Functionalized Poly Alkyl Glucosides as Enhancers for Laundry Soil Removal, describes the use of blends of functionalized alkyl polyglucosides in laundry and spot removal applications.
  • PCT Application PCT/US20/62184 Citrate- Functionalized Polymeric Surfactants Based Upon Alkyl Polyglucosides, describes a new class of functionalized alkyl polyglucosides that can be used in the lot of these cleansing applications.
  • Thickeners are often used in combination to give an acceptable consistency, with gums such as xanthan or carrageenan being used together with thickening silicas to achieve the desired results.
  • Humectants act primarily to help water retention within the toothpaste formulation over time and, as with thickeners, also affect longer-term toothpaste stability and toothpaste consistency during use.
  • Water is one of the main ingredients of most toothpastes and is important for effective fluoride delivery. In addition to this, good water retention will usually give gloss or shine to the formulation and give a more appealing texture to the toothpaste within the mouth.
  • Humectants such as glycerol, sorbitol and polyethylene glycol are typically used to achieve this; all of these have been used for many years in toothpaste formulations for adults and children. These ingredients often also serve other functions in the toothpaste, as most convey some level of sweetness, which is important in compatibility with the flavors for a children’s toothpaste.
  • Surfactants provide foam during brushing, which helps with wetting of the tooth surfaces, dispersion of the toothpaste in the mouth and with loosening of debris and plaque from tissues of the mouth.
  • Choice of surfactant type and concentration for toothpaste is important so as to minimize any potential for irritation of oral soft tissue, and to minimize any negative affect on fluoride availability. Additional surfactants can be added to the compositions of the present invention.
  • Flavor is used in toothpaste formulations to make the taste and odor of the product appealing during and after use. Different flavor components can give breath-freshening benefits by masking odors and can provide cooling or warming sensations within the mouth during and after brushing. Flavors can also serve to mask the taste of other ingredients in the toothpaste formulation. Sweeteners, such as sodium saccharin, sucralose and xylitol, work together with the flavor system by adding a degree of sweetness to the toothpaste but avoid the use of fermentable sugars. Xylitol likely has anti-caries potential when delivered continuously from chewing gum and confectionary, although when delivered from toothpaste, evidence for this is inconclusive at present.
  • fluoride salts are used in toothpaste such as sodium fluoride, sodium monofluorophosphate, amine fluoride and stannous fluoride.
  • the main oral health benefit of brushing with fluoride toothpastes is the delivery of fluoride to the mouth.
  • plaque buffers such as urea, calcium lactate, calcium glycerophosphate and strontium polyacrylates
  • anti-inflammatory agents such as ibuprofen, flurbiprofen, aspirin, and indomethacin
  • desensitizing agents such as potassium citrate, potassium chloride, potassium tartrate, potassium bicarbonate, potassium oxalate, potassium nitrate and strontium salts
  • anti-calculus agents such as alkali-metal pyrophosphates, hypophosphite-containing polymers, organic phosphonates and phosphocitrates
  • bio-molecules such as bacteriocins, antibodies, and enzymes
  • proteinaceous materials such as collagen; preservatives; opacifying agents; coloring agents; pH-adjusting agents; sweetening agents, such as saccharin and sorbitol (vide supra); bleaching agents, such as peroxy compounds (e.g.
  • potassium peroxydiphosphate buffers and salts to buffer the pH and ionic strength of the composition
  • pharmaceutically acceptable carriers e g. starch, sucrose, water or water/alcohol systems.
  • Water is a particularly preferred pharmaceutically acceptable carrier and is typically present in compositions of the invention at from 5 to 95%, in particular 15 to 75%, and especially at from 35 to 60% by weight of the total composition.
  • mouthwashes are generally classified as either cosmetic or therapeutic or a combination of the two.
  • Cosmetic rinses are commercial products that remove oral debris before or after brushing, temporary suppress bad breath, diminish bacteria in the mouth and refresh the mouth with a pleasant taste.
  • Therapeutic rinses often have the benefits of their cosmetic counterparts, but also contain an added active ingredient, (for example fluoride or chlorhexidine), that help protect against some oral diseases.
  • active ingredient for example fluoride or chlorhexidine
  • the amount of the different ingredients in mouthwashes varies from product to product. Some practically have the same composition as toothpastes, although they do not contain abrasives. Distinct from toothpastes most mouth-washes contain alcohol, as a preservative and a semi-active ingredient. The amount of alcohol is usually ranging from 18 - 26 %.
  • Suga®Nate 160NC has been tested for its oral and gingival irritation potential in vitro (MatTek EpiOralTM & EpiGingivalTM). The results indicate that Suga®Nate 160NC does not have the potential to cause oral or gingival irritation neither as a 4% solution nor as a neat product (no ET-50 can be calculated). 2% SLS, a commonly used surfactant in toothpaste formulations, resulted in gingival irritation (ET-50 of 418.2 minutes). Taken together, the results reveal that Suga®Nate 160NC, even as a neat product, is less irritating to oral and gingival tissues than 2% SLS. This data has been integrated into a wider safety assessment which concluded that Suga®Nate 160NC has a safety profile that is favorable to its use in oral care products.
  • Example toothpaste and mouthwash formulations using Suga®Nate 160NC were prepared and are shown below in Tables 1 and 2.
  • Other acceptable ingredients that could be used in mouthwashes include a sweetener, a flavoring agent, a coloring agent, a dispersing agent, a thickening agent, enzymes, an anionic surfactant, a nonionic surfactant, an anti-plaque ingredient, an antimicrobial agent, a calcium ion source, a phosphate ion source, a fluoride source, anti-sensitive teeth agents, water- soluble organic alcohols or glycols, and water.
  • a sweetener a flavoring agent, a coloring agent, a dispersing agent, a thickening agent, enzymes, an anionic surfactant, a nonionic surfactant, an anti-plaque ingredient, an antimicrobial agent, a calcium ion source, a phosphate ion source, a fluoride source, anti-sensitive teeth agents, water- soluble organic alcohols or glycols, and water.
  • Poly Suga ® Nate 160P NC described as sodium hydroxypropyl sulfonate laurylglucoside crosspolymer, has a similar eye and skin safety profile as Suga®Nate 160NC. Eye Irritation:
  • MatTek Epi-Ocular In vitro epidermal keratinocytes: Results indicate ‘non- irritating’ classification (ET-50: 256 min+).
  • Poly Suga ® Mulse D9 described as sorbitan oleate decylglucoside crosspolymer, has a similar safety profile to other functionalized alkyl polyglucosides described herein. Eye Irritation:
  • MatTek EpiOcularTM In vitroepidermal keratinocytes'. Results indicate a ‘nonirritating’ classification (ET-50: 256min+).
  • HET-CAM - Hen s Egg Chorioallantoic Membrane Test, practically no ocular irritation, rated 2.25.
  • dates of publication provided herein can be different from the actual publication dates, which need to be independently confirmed.
  • Ranges can be expressed herein as from “about” one particular value, and/or to
  • Compounds described herein can contain one or more double bonds and, thus, potentially give rise to cis/trans (E/Z) isomers, as well as other conformational isomers. Unless stated to the contrary, the invention includes all such possible isomers, as well as mixtures of such isomers. As stated above, the compounds described herein specifically include positional isomers.
  • a formula with chemical bonds shown only as solid lines and not as wedges or dashed lines contemplates each possible isomer, e.g., each enantiomer and diastereomer, and a mixture of isomers, such as a racemic or scalemic mixture.
  • Compounds described herein can contain one or more asymmetric centers and, thus, potentially give rise to diastereomers and optical isomers.
  • the present invention includes all such possible diastereomers as well as their racemic mixtures, their substantially pure resolved enantiomers, all possible geometric isomers, and pharmaceutically acceptable salts thereof. Mixtures of stereoisomers, as well as isolated specific stereoisomers, are also included.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)
EP22825973.5A 2021-06-18 2022-06-21 Sulfonatfunktionalisierte alkylpolyglucoside als sulfatfreie tenside für zahnpasta und mundwasser Pending EP4355435A1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US202163212558P 2021-06-18 2021-06-18
PCT/US2022/034403 WO2022266548A1 (en) 2021-06-18 2022-06-21 Sulfonate-functionalized alkyl polyglucosides as sulfate-free surfactants for toothpaste and mouthwash

Publications (1)

Publication Number Publication Date
EP4355435A1 true EP4355435A1 (de) 2024-04-24

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ID=84526558

Family Applications (1)

Application Number Title Priority Date Filing Date
EP22825973.5A Pending EP4355435A1 (de) 2021-06-18 2022-06-21 Sulfonatfunktionalisierte alkylpolyglucoside als sulfatfreie tenside für zahnpasta und mundwasser

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EP (1) EP4355435A1 (de)
WO (1) WO2022266548A1 (de)

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7087571B1 (en) * 2005-01-25 2006-08-08 Colonial Chemical Alkyl polyglycoside derived sulfosuccinates
US8268766B1 (en) * 2009-09-11 2012-09-18 Surfatech Corporation Polymeric surfactants based upon alkyl polyglycosides and sorbitan esters
US8071520B2 (en) * 2009-11-06 2011-12-06 Ecolab Usa Inc. Sulfonated alkyl polyglucoside use for enhanced food soil removal
US20120046215A1 (en) * 2010-08-23 2012-02-23 Ecolab Usa Inc. Poly sulfonate functionalized alkyl polyglucosides for enhanced food soil removal
EP3435958A1 (de) * 2016-04-01 2019-02-06 The Procter and Gamble Company Mundpflegezusammensetzungen mit gelnetzwerkphase und kaliumnitrat
CN112770712A (zh) * 2018-08-27 2021-05-07 巴斯夫欧洲公司 口腔摩丝组合物
WO2020210549A1 (en) * 2019-04-09 2020-10-15 Colonial Chemical, Inc. Sugar-based, environmentally-friendly surfactants for emulsion polymerization
WO2021062404A1 (en) * 2019-09-26 2021-04-01 Colonial Chemical, Inc. Blends of functionalized poly alkyl glucosides for laundry soil removal

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